有机化学 ›› 2021, Vol. 41 ›› Issue (1): 348-356.DOI: 10.6023/cjoc202006036 上一篇    下一篇

所属专题: 有机硅化学合辑

研究论文

二苯基八氢吲哚醇硅醚催化α,β-不饱和醛不对称[3+3] 氮杂环化反应合成苯并呋喃衍生物

温慧玲a, 罗年华a, 欧阳露a, 罗人仕a,*()   

  1. a 赣南医学院药学院 江西赣州 341000
  • 收稿日期:2020-06-19 修回日期:2020-08-09 发布日期:2020-08-27
  • 通讯作者: 罗人仕
  • 作者简介:
    * Corresponding author. E-mail:
  • 基金资助:
    国家自然科学基金(21962004); 国家自然科学基金(21562004); 江西省自然科学基金(20192BAB203004); 江西省教育厅(GJJ190829); 赣南医学院(QD201832); 赣南医学院(QD201816); 赣南医学院(YJ202027)

Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric [3+3] Aza-cyclization ofα,β-Unsaturated Aldehydes

Huiling Wena, Nianhua Luoa, Lu Ouyanga, Renshi Luoa,*()   

  1. a School of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000
  • Received:2020-06-19 Revised:2020-08-09 Published:2020-08-27
  • Contact: Renshi Luo
  • Supported by:
    the National Natural Science Foundation of China(21962004); the National Natural Science Foundation of China(21562004); the Jiangxi Provincial Department of Science and Technology(20192BAB203004); the Foundation of Jiangxi Provincial Department of Education(GJJ190829); Gannan Medical University(QD201832); Gannan Medical University(QD201816); Gannan Medical University(YJ202027)

二苯基八氢吲哚醇硅醚可高对映选择性催化3-氨基苯并呋喃与 α, β-不饱和醛的[3+3]氮杂环化反应, 获得高收率(高达93%)、高非对映选择性( dr>20∶1)和高对映选择性(86%~>99% ee)的苯并呋喃衍生物. 该方法可获得克级规模的苯并呋喃衍生物.

关键词: 关键词 二苯基八氢吲哚醇硅醚, [3+3]氮杂环化αβ-不饱和醛, 3-氨基苯并呋喃

A highly enantioselective [3+3] aza-cyclization of α, β-unsaturated aldehydes with 3-aminobenzofuran promoted by diphenylperhydroindolinol silyl ether has been described, which afforded benzofuran derivatives in high yields (up to 93%), diastereoselectivities ( dr>20∶1) and enantioselectivities (86%~>99% ee). This method also enabled to obtain benzofuran derivatives in gram scale-up.

Key words: diphenylperhydroindolinol silyl ether, [3+3] aza-cyclizationαβ-unsaturated aldehydes, 3-aminobenzofuran